Meet Wild Web Woman, Jody Stephenson

Jody Stephenson is the founder of The Sitter Tree, a local Atlanta babysitting community. The Sitter Tree makes finding reliable, quality babysitters easy. Their coordinators fill 99.9% of all sitter requests, even last-minute requests. As a member of The Sitter Tree, moms can sit back and let the coordinators do the work. Local coordinators recruit, interview, background check, and manage their roster of nearly 1,000 sitters. They do everything a mom would do when searching for a sitter, which is why they only approve one in five applicants, and which is why their sitters currently average 97% 5-star ratings from Atlanta moms.

Meet Jody!

What inspired you to launch your web-based business? I was a college student and needed a job which would pay more than the minimum wage I was earning working in the library. I have always loved children, so I started babysitting. Eventually, I had index cards and excel sheets to organize sitters for other families. I was assigning my friends, so I knew the families were having a great experience. I finally realized I could serve a lot more families – and create a lot more jobs for college students – if I could create a web tool to automate some of the work. And, so it began.

How has your previous employment experience aided you professionally? Previously, I coordinated volunteer teams serving overseas. Not only was I working with people and logistics, but I was coordinating them on an international basis, which complicates things. I was also coordinating for up to 1,000 people each year. I learned how to create systems, and more importantly, which functions of the system to automate, and which functions need human touch. It’s also where I learned everyone has unspoken expectations, even on short-term service trips.

Do you weave your values into your business? Most certainly. This is my favorite part of my job. I care deeply about people, families, and our city. You can’t automate genuine care and concern. I wanted to build a business which prioritized genuine care about and for people. My hope has been that I can create a ripple effect as I exemplify this to our coordinators. In turn, they demonstrate this to every sitter they interview – whether they approve the sitter, or not. From there our sitters pass this on to the kids and families that they meet. Finally- people may forget this, but it’s significant– I hope our families take the time to genuinely care about the sitters who come into their homes.

What is the best part about being a web-based businesswoman? The possibilities are endless. The Sitter Tree can reach as far as the web can. Being web-based means you have the potential to, literally, reach the world.

What is the most challenging part of being a web-based businesswoman? The web can be a noisy space. And, I would imagine many women are like me in that they absorb quite a bit of the noise, they sort it, order it, and manage it. The thing is, the noise doesn’t stop at 5pm. So, while the possibilities are endless, your time and your life aren’t, and if you don’t choose to stop, to slow down, and to live within the limits we all have, we’ll miss out on life. But, the tension is always there.

What is your favorite way to unplug from work? Definitely a walk on one of Atlanta’s beautiful outdoor trails. Or, I love, love, love competitive team sports. I will play volleyball, basketball or tennis with friends. To really unplug, I pack my bags, grab a few friends and head overseas. There’s something about other cultures- people, food, art, music, which clears my mind and gets my creative juices going.

How do you maintain your health? I value my mind, body and spirit, and I prioritize all of them. Sometimes more than others. I rest my mind by taking walks 3-5 times per week, or by watching an episode of The Office and laughing out loud. I pay attention to the amount of sleep I need and if I am fueling my body with good food. And, I am part of a church community, where I am reminded I am part of a much bigger story, and to keep that in mind when making decisions.

What are some of your proudest accomplishments? My proudest accomplishments are more related to relationships and resilience than a specific job. All of my jobs have involved relationships and have contributed to the development of resilience. I am proud to be a good friend, over many years with many people of all walks of life. I am proud to have failed and failed again, and to have re-engaged myself. I am proud to have reached a place of lower expectations for others and myself (my 20s were brutal!), and to take on challenges with a fresh sense of expectancy and acceptance that things may go completely sideways. Even then, it will be interesting to see what comes of it all!

What is the wildest thing you have ever done? I signed up to move to Malawi right out of college. I was going to work with an organization serving orphaned children, and I was so moved, I packed my bags and boarded a plane without ever having met anyone from the organization.

What three web tools can you not live without?Google Drive. OMG I love Drive. Also, because I can’t live without my coordinators, I have to say Boomerang and Calendly. It’s quite possible I would lose every employee if I canceled our subscription to either. Both tools keep us organized and ensure we follow up on any loose ends- and, this is one team which loves to be organized.

What helps you increase your productivity the most? Here is where the coordinators may not be so happy with me- Toggl. Tracking time, while it can be a nuisance, is so valuable. Not only does it help you fill the moments you may have waited for a response from someone, but it can also help you stop working, once you have billed your hours and are just logging back in to check one more thing, which really could wait until tomorrow. I have a statement on the top of my whiteboard in my office “Don’t work when you don’t have to.” Working more than you need to, while it can look impressive to others, can actually lower productivity, in my experience.

Do you have any personal “wild web” role models? If so, who? I am a bit of a nerd when it comes to case studies and podcasts and interviews with the wild web founders who started small, doing very unscalable things, and then… 100 million users later are reflecting and talking about their journey. One particular Masters of Scale podcast I enjoyed was an interview with Brian Chesky from AirBNB. The episode “Handcrafted” made my mind race with ideas and my heart race with excitement to try them!

What are some risks you have taken that resulted in positive outcomes? I took an investor. This was a big step to give up control. I am so good when I have everything in my control. 🙂 But, it was the best decision I have made because of who I selected. The original investor has acted as a partner in many ways. I didn’t have a co-founder, but giving up control and part of my company to the right person has most definitely allowed us to come this far.

What is the most important lesson you’ve learned in your career to date? Own it. Own your mistakes- everyone makes them. But, more importantly, own your strengths. Don’t base your worth on either. But, be comfortable knowing this is your skill set, what you bring to the team, and each of your team members brings something, as well. It seems more difficult to appreciate – with confidence- someone else’s strengths until you can own your own. Previously, I may have been more prone to compare myself to someone else and what I perceived they had that I didn’t. Now, I am more prone to just own the mixed bag of strengths and “opportunities” I come with.

How do you maintain a work/life balance? I establish routines. It’s back to the basics for me. I am a person who loves routines. They offer predictability, which reduces stress in my world. Also, I take the time to travel for extended periods of time. A significant advantage to being a wild web woman is mobility. It turns out, life is not just about productivity. Sometimes that’s much better understood with a cappuccino in hand at a Dutch cafe.

Business-wise, where do you see yourself in ten years? The Sitter Tree is at a pivotal point. The next three years will determine quite a lot for us, and for me. Whether I am with The Sitter Tree or another venture, I want to love what I do, work hard at doing it, and to do it with people I respect and care about.

Where’s your favorite place to work from? My kitchen counter or a shared office space when I want a bit more interaction. Unfortunately, workout clothes are often frowned upon in shared office spaces.

How do you make your home a productive space to work? I don’t struggle with this. Once I open my computer, it’s game on.

What is the #1 piece of advice would you give to someone who’s aspiring to run a web-based business and be a Wild Web Woman? It comes down to a good idea, a great team, and a commitment to always remain a learner. I would make a broad sweeping over-confident statement that a number of great ideas don’t make it because they don’t have a great team and/or because they are too inward focused. If you, as a founder, don’t have the desire and ability to a) surround yourself with other great minds, b) learn from them, and c) put effort into studying what others are doing/have done, then you might be your company’s biggest threat. Don’t be a maverick. Surround yourself with good people, who bring other great ideas to yours, and navigate the wild web together!

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Web-based businesses RULE!

Being a wild web woman means doing the work you love and embracing the flexibility to live the life you want AND deserve! Success doesn't happen in a silo, the WWW community of webpreneur women are here to help! You CAN have it all - a solid web-based business is the foundation! Hit the blue icon below to subscribe to our fun and fab advice! When you do, you get happy, healthy and wealthy tips delivered to you automagically!

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Wild Web Women® (WWW) is a virtual support system for women who run web-based businesses teaching everything from sales, marketing, operations, management and life balance (yes, there is such a thing).

WWW was created by a team of women who have run a successful web-based business for over a decade. Web-based businesses RULE! Without the wild, wonderful web, we wouldn’t have been able to raise our families, run our households, volunteer, travel and make money honey!